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Cucurbitacin Ⅱa

$225

  • Brand : BIOFRON

  • Catalogue Number : BF-C4010

  • Specification : 98%(HPLC)

  • CAS number : 58546-34-2

  • Formula : C32H50O8

  • Molecular Weight : 562.73

  • PUBCHEM ID : 181183

  • Volume : 25mg

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Catalogue Number

BF-C4010

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

562.73

Appearance

White crystalline powder

Botanical Source

Hemsleya chinensis

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC(=O)OC(C)(C)CCC(=O)C(C)(C1C(CC2(C1(CC(=O)C3(C2CC=C4C3CC(C(C4(C)C)O)O)C)C)C)O)O

Synonyms

23,24-Dihydrocucurbitacin F-25-O-acetate/19-Norlanost-5-ene-11,22-dione, 25-(acetyloxy)-2,3,16,20-tetrahydroxy-9-methyl-, (2β,3α,9β,10α,16α)-/Curcurbitacin Q1/(1S,2S,4R,9β,16α)-1,2,16,20-Tetrahydroxy-9,10,14-trimethyl-11,22-dioxo-4,9-cyclo-9,10-secocholest-5-en-25-yl acetate/Estr-5-en-11-one, 17-[(1R)-5-(acetyloxy)-1-hydroxy-1,5-dimethyl-2-oxohexyl]-2,3,16-trihydroxy-4,4,9,14-tetramethyl-, (2β,3α,9β,10α,16α,17β)-/Dihydrocucurbitacin F 25-O-acetate/X1160/Dihydrocucurbitacin Q1/25-O-Acetyl-23,24-dihydrocucurbitacin F/Cucurbitacin IIa/Hemslecin A

IUPAC Name

[(6R)-6-hydroxy-2-methyl-5-oxo-6-[(2S,3S,8S,9R,10R,13R,14S,16R,17R)-2,3,16-trihydroxy-4,4,9,13,14-pentamethyl-11-oxo-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]heptan-2-yl] acetate

Density

1.2±0.1 g/cm3

Solubility

Methanol

Flash Point

209.7±25.0 °C

Boiling Point

679.1±55.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C32H50O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,19-22,25-26,34-35,38-39H,11-16H2,1-9H3/t19-,20+,21-,22+,25+,26-,29+,30-,31+,32+/m1/s1

InChl Key

LKYNAQSYQLFTCM-GYXNDICUSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:58546-34-2) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31265865

Abstract

Cucurbitacin IIa (CuIIa), a tetracyclic triterpenoid harboring anticancer activity, was investigated in A549 cells to reveal its mechanism of targeting on epidermal growth factor receptor (EGFR) signaling pathway. Results showed that CuIIa was capable of inducing apoptosis and cell cycle arrest at G2/M phase. The transcription of EGFR pathway genes and their proteins accumulation was inconsistently influenced by CuIIa. Notably, transcription of Raf1 was significantly upregulated, nevertheless, MEK1 and ERK1 were significantly downregulated. On the other hand, the accumulation of the total and phosphorylated proteins of the most members in EGFR-mitogen-activated protein kinase (MAPK) pathway, as well as CylclinB1 and survivin were also shifted by CuIIa treatment. Remarkably, total MEK remained constant but survivin completely degraded. Moreover, phosphorylated BRAF continuously increased while Raf1 and MEK decreased continuously. CuIIa was further confirmed to be a tyrosine kinase inhibitor (TKI) of EGFR by kinase inhibition assay. The results of molecular simulation showed that the long side chain of CuIIa occupied the binding pocket of EGFR and the ligand was stabilized at the active site of EGFR. In view of the results above, it is suggested that CuIIa inhibits cell proliferation by interfering the EGFR-MAPK signaling pathway.

Copyright © 2019 Elsevier Ltd. All rights reserved.

KEYWORDS

Apoptosis; Cell cycle arrest; Cucurbitacin; Epidermal growth factor receptor; Molecular simulation

Title

Cucurbitacin IIa interferes with EGFR-MAPK signaling pathway leads to proliferation inhibition in A549 cells.

Author

Zhang J1, Song Y1, Liang Y1, Zou H1, Zuo P2, Yan M1, Jing S1, Li T2, Wang Y2, Li D2, Zhang T3, Wei Z4.

Publish date

2019 Oct


Description :

Cucurbitacin IIa is a triterpene isolated from Hemsleya amalils Diels, induces apoptosis of cancer cells, reduces expression of survivin, reduces phospho-Histone H3 and increases cleaved PARP in cancer cells[1].